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The title compound, (C6H5CH2)3PO, is an organic tertiary phosphine oxide. The mol­ecule has threefold symmetry, with the P-O bond along the threefold axis. Main dimensions include P-O 1.488 (4), P-C 1.823 (3) Å and O-P-C 114.7 (1)°. The crystals were accidentally obtained when preparing complexes of nickel(II) with di­benzyl­phosphine.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001566/qb0179sup1.cif
Contains datablocks X, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001566/qb0179Isup2.hkl
Contains datablock I

CCDC reference: 143332

Comment top

The title compound, (I), is an organic phosphorus compound that belongs to a type of tertiary phosphine oxides. In the final stages of the synthesis of dihalogenobis(tribenzylphosphine)nickel(II) complexes (Pérez et al., 1998), (I) was isolated as colourless needles, possibly formed by an oxidation process due to atmospheric oxygen. The P—O distance agrees with the mean distance of 1.50 Å calculated by Bye et al. (1982), based on 62 Ph3PO fragments. The P—C and C—C distances are similar to those found in compounds with tribenzylphosphine groups (Kilbourn & Powell, 1970). The two torsion angles P1—C3—C4—Ci (i = 5 and 9) show that the three benzyl groups differ by aproximatelly 180°. The molecules are packed at normal van der Waals distances.

Experimental top

In the recrystallization of dihalogenobis(tribenzylphosphine)nickel(II) from dichloromethane–butanol (1:1) under an oxygen atmosphere (Pérez et al., 1998), colorless needles of the title compound were obtained.

Refinement top

H atoms were calculated geometrically and included in the refinement, but were restrained to ride on their parent atoms. The isotropic displacement parameters of the H atoms were fixed to 1.3 times Ueq of their parent atoms.

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: PARST (Nardelli, 1983).

tribenzylphosphine oxide top
Crystal data top
C21H21OPDx = 1.211 Mg m3
Mr = 320.35Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 30 reflections
a = 16.685 (2) Åθ = 13.8–27.9°
c = 5.468 (1) ŵ = 0.16 mm1
V = 1318.3 (3) Å3T = 293 K
Z = 3Prism, colourless
F(000) = 5100.56 × 0.32 × 0.20 mm
Data collection top
Stoe STADI-4 four-circle
diffractometer
Rint = 0.035
ω scansθmax = 24.9°
Absorption correction: ψ scan
(EMPIR; Stoe & Cie, 1992)
h = 1919
Tmin = 0.913, Tmax = 0.969k = 1919
5177 measured reflectionsl = 06
578 independent reflections2 standard reflections every 60 min
558 reflections with F2 > 2σ(F2) intensity decay: 0.0%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0568P)2 + 0.3906P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.032(Δ/σ)max = 0.001
wR(F2) = 0.088Δρmax = 0.11 e Å3
S = 1.07Δρmin = 0.12 e Å3
578 reflectionsAbsolute structure: Flack (1983)
70 parametersAbsolute structure parameter: 0.1 (2)
Crystal data top
C21H21OPZ = 3
Mr = 320.35Mo Kα radiation
Trigonal, R3µ = 0.16 mm1
a = 16.685 (2) ÅT = 293 K
c = 5.468 (1) Å0.56 × 0.32 × 0.20 mm
V = 1318.3 (3) Å3
Data collection top
Stoe STADI-4 four-circle
diffractometer
558 reflections with F2 > 2σ(F2)
Absorption correction: ψ scan
(EMPIR; Stoe & Cie, 1992)
Rint = 0.035
Tmin = 0.913, Tmax = 0.9692 standard reflections every 60 min
5177 measured reflections intensity decay: 0.0%
578 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.088Δρmax = 0.11 e Å3
S = 1.07Δρmin = 0.12 e Å3
578 reflectionsAbsolute structure: Flack (1983)
70 parametersAbsolute structure parameter: 0.1 (2)
Special details top

Refinement. The structure was solved by direct methods and Fourier synthesis. Non-H atoms were refined anisotropically by full-matrix least-squares techniques. H atoms were calculated geometrically and included in the refinement, but were restrained to ride on their parent atoms. The isotropic displacement parameters of the H atoms were fixed to 1.3 times Ueq of their parent atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P11.000000.000000.06651 (14)0.0428 (3)
O11.000000.000000.2056 (7)0.0642 (9)
C31.01310 (19)0.10515 (19)0.2058 (6)0.0506 (8)
C40.9339 (2)0.1221 (2)0.1568 (5)0.0519 (9)
C50.8622 (3)0.0922 (2)0.3190 (10)0.0762 (13)
C60.7891 (3)0.1080 (4)0.2739 (16)0.114 (3)
C70.7875 (5)0.1520 (7)0.0731 (18)0.148 (3)
C80.8578 (7)0.1819 (7)0.0891 (11)0.155 (4)
C90.9323 (5)0.1680 (5)0.0499 (8)0.103 (2)
H3A1.019560.101750.381200.0657*
H3B1.069730.157610.145440.0657*
H50.862270.061210.460200.0992*
H60.740780.087420.385720.1484*
H70.738360.162130.044350.1925*
H80.856240.212420.229910.2022*
H90.980540.189600.162310.1348*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0441 (4)0.0441 (4)0.0402 (5)0.0221 (2)0.00000.0000
O10.0738 (14)0.0738 (14)0.045 (2)0.0369 (7)0.00000.0000
C30.0493 (14)0.0433 (14)0.0576 (16)0.0220 (11)0.0052 (13)0.0040 (12)
C40.0550 (16)0.0497 (14)0.0550 (17)0.0291 (12)0.0057 (13)0.0100 (13)
C50.066 (2)0.0575 (17)0.105 (3)0.0307 (16)0.020 (2)0.0084 (19)
C60.054 (2)0.092 (3)0.191 (7)0.033 (2)0.001 (3)0.059 (4)
C70.138 (5)0.204 (7)0.178 (6)0.143 (6)0.101 (5)0.130 (6)
C80.253 (9)0.266 (9)0.085 (3)0.233 (9)0.043 (5)0.035 (5)
C90.155 (4)0.159 (5)0.066 (2)0.131 (4)0.005 (3)0.011 (3)
Geometric parameters (Å, º) top
P1—O11.488 (4)C5—H50.930
P1—C31.823 (3)C6—C71.33 (1)
C4—C31.508 (6)C6—H60.930
C4—C51.367 (5)C9—C81.39 (2)
C4—C91.373 (7)C9—H90.930
C3—H3A0.970C7—C81.35 (1)
C3—H3B0.970C7—H70.930
C5—C61.392 (8)C8—H80.930
O1—P1—C3114.7 (1)C5—C6—C7120.8 (7)
C3—C4—C5120.4 (3)C5—C6—H6119.6
C3—C4—C9120.9 (4)C7—C6—H6119.6
C5—C4—C9118.7 (4)C4—C9—C8119.2 (6)
P1—C3—C4114.3 (2)C4—C9—H9120.4
P1—C3—H3A108.7C8—C9—H9120.4
P1—C3—H3B108.7C6—C7—C8119.6 (9)
C4—C3—H3A108.7C6—C7—H7120.2
C4—C3—H3B108.7C8—C7—H7120.2
H3A—C3—H3B107.6C9—C8—C7121 (1)
C4—C5—C6120.4 (4)C9—C8—H8119.3
C4—C5—H5119.8C7—C8—H8119.3
C6—C5—H5119.8
O1—P1—C3—C465.0 (3)C4—C5—C6—C70 (1)
O1—P1—C3—H3A173.4C4—C5—C6—H6179.9
O1—P1—C3—H3B56.6H5—C5—C6—C7179.9
C5—C4—C3—P193.6 (4)H5—C5—C6—H60.1
C5—C4—C3—H3A27.9C5—C6—C7—C80 (1)
C5—C4—C3—H3B144.8C5—C6—C7—H7179.9
C9—C4—C3—P186.7 (4)H6—C6—C7—C8179.9
C9—C4—C3—H3A151.7H6—C6—C7—H70.1
C9—C4—C3—H3B34.9C4—C9—C8—C71 (1)
C3—C4—C5—C6179.9 (4)C4—C9—C8—H8179.3
C3—C4—C5—H50.1H9—C9—C8—C7179.3
C9—C4—C5—C60.3 (7)H9—C9—C8—H80.7
C9—C4—C5—H5179.8C6—C7—C8—C90 (1)
C3—C4—C9—C8179.7 (6)C6—C7—C8—H8179.7
C3—C4—C9—H90.3H7—C7—C8—C9179.7
C5—C4—C9—C80.6 (9)H7—C7—C8—H80.3
C5—C4—C9—H9179.4

Experimental details

Crystal data
Chemical formulaC21H21OP
Mr320.35
Crystal system, space groupTrigonal, R3
Temperature (K)293
a, c (Å)16.685 (2), 5.468 (1)
V3)1318.3 (3)
Z3
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.56 × 0.32 × 0.20
Data collection
DiffractometerStoe STADI-4 four-circle
diffractometer
Absorption correctionψ scan
(EMPIR; Stoe & Cie, 1992)
Tmin, Tmax0.913, 0.969
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
5177, 578, 558
Rint0.035
(sin θ/λ)max1)0.592
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.088, 1.07
No. of reflections578
No. of parameters70
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.11, 0.12
Absolute structureFlack (1983)
Absolute structure parameter0.1 (2)

Computer programs: DIF4 (Stoe & Cie, 1992), DIF4, REDU4 (Stoe & Cie, 1992), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PARST (Nardelli, 1983).

Selected geometric parameters (Å, º) top
P1—O11.488 (4)C4—C31.508 (6)
P1—C31.823 (3)
O1—P1—C3114.7 (1)C3—C4—C9120.9 (4)
C3—C4—C5120.4 (3)P1—C3—C4114.3 (2)
O1—P1—C3—C465.0 (3)C9—C4—C3—P186.7 (4)
C5—C4—C3—P193.6 (4)
 

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